Cheap Flights from Milan to Chicago, IL from $412

Return flight: Chicago – Milan

On Cheapflightsplus.com you will find 2 direct and 152 connecting flights from Milan to Chicago. You can compare airfare deals from 28 airlines and multiple travel sites from $412, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Milan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $412 (one-way), $707 (round-trip).
Direct flights
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Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
15:20 — 18:10
15:20 — 18:10 LH7812 Lufthansa
Milan — Chicago
9h 50m
Find flight
from$1530
15:20 — 18:10
15:20 — 18:10 UA415 United Airlines
Milan — Chicago
9h 50m
Find flight
from$1601
06:50 — 17:55
07:00 — 12:00 TK1878 Turkish Airlines
Milan — Istanbul
3h 35m stop
15:30 — 18:25 TK5 Turkish Airlines
Istanbul — Chicago
18h 5m
including layover
Find flight
from$556
06:50 — 22:00
06:50 — 10:50 TK1878 Turkish Airlines
Milan — Istanbul
7h 55m stop
18:45 — 22:00 TK155 Turkish Airlines
Istanbul — Chicago
22h 10m
including layover
Find flight
from$558
07:25 — 15:55
07:25 — 08:30 BA561 British Airways
Milan — London
4h 40m stop
13:10 — 15:55 BA299 British Airways
London — Chicago
15h 30m
including layover
Find flight
from$423
07:25 — 18:15
07:35 — 08:50 BA561 British Airways
Milan — London
7h stop
15:45 — 18:45 BA297 British Airways
London — Chicago
17h 50m
including layover
Find flight
from$423
08:30 — 18:15
07:15 — 10:50 U23969 EasyJet
Milan — Reykjavik
5h 30m stop
16:45 — 17:20 FI853 Icelandair
Reykjavik — Chicago
16h 45m
including layover
Find flight
from$733
10:45 — 09:40
+1 day
11:10 — 16:10 TK1874 Turkish Airlines
Milan — Istanbul
15h 45m stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
29h 55m
including layover
Find flight
from$557
10:45 — 17:55
+1 day
11:10 — 16:10 TK1874 Turkish Airlines
Milan — Istanbul
23h 40m stop
15:30 — 18:25 TK5 Turkish Airlines
Istanbul — Chicago
38h 10m
including layover
Find flight
from$557
11:20 — 19:00
11:20 — 12:55 EI433 Aer Lingus
Milan — Dublin
3h 40m stop
16:40 — 19:00 EI125 Aer Lingus
Dublin — Chicago
14h 40m
including layover
Find flight
from$463
13:05 — 13:10
+1 day
13:00 — 14:10 AZ2133 Alitalia
Milan — Rome
19h 10m stop
09:25 — 13:10 AZ628 Alitalia
Rome — Chicago
31h 5m
including layover
Find flight
from$675
13:20 — 20:13
13:20 — 16:20 BA1623 British Airways
Milan — Philadelphia
2h 17m stop
18:45 — 20:22 BA5702 British Airways
Philadelphia — Chicago
13h 53m
including layover
Find flight
from$661
14:00 — 13:10
+1 day
14:00 — 15:10 AZ2049 Alitalia
Milan — Rome
18h 15m stop
09:25 — 13:10 AZ628 Alitalia
Rome — Chicago
30h 10m
including layover
Find flight
from$675
14:55 — 14:15
+1 day
14:25 — 16:50 IB674 Iberia
Milan — Madrid
18h 15m stop
11:35 — 14:15 IB341 Iberia
Madrid — Chicago
30h 20m
including layover
Find flight
from$484
15:10 — 09:40
+1 day
14:40 — 19:35 TK1896 Turkish Airlines
Milan — Istanbul
11h 20m stop
07:35 — 10:10 TK185 Turkish Airlines
Istanbul — Chicago
25h 30m
including layover
Find flight
from$558
15:10 — 17:55
+1 day
14:40 — 19:35 TK1896 Turkish Airlines
Milan — Istanbul
19h 15m stop
15:30 — 18:25 TK5 Turkish Airlines
Istanbul — Chicago
33h 45m
including layover
Find flight
from$558
17:00 — 13:10
+1 day
17:00 — 18:10 AZ2061 Alitalia
Milan — Rome
15h 15m stop
09:25 — 13:10 AZ628 Alitalia
Rome — Chicago
27h 10m
including layover
Find flight
from$675
19:00 — 13:10
+1 day
19:00 — 20:10 AZ2109 Alitalia
Milan — Rome
13h 15m stop
09:25 — 13:10 AZ628 Alitalia
Rome — Chicago
25h 10m
including layover
Find flight
from$675
19:05 — 14:15
+1 day
19:05 — 21:30 IB676 Iberia
Milan — Madrid
14h 5m stop
11:35 — 14:15 IB341 Iberia
Madrid — Chicago
26h 10m
including layover
Find flight
from$534
20:20 — 14:15
+1 day
20:25 — 22:50 IB666 Iberia
Milan — Madrid
12h 55m stop
11:35 — 14:30 AY5659 Finnair
Madrid — Chicago
24h 55m
including layover
Find flight
from$449
20:20 — 14:15
+1 day
20:20 — 22:40 IB666 Iberia
Milan — Madrid
12h 55m stop
11:35 — 14:15 IB341 Iberia
Madrid — Chicago
24h 55m
including layover
Find flight
from$540
08:30 — 17:25
07:00 — 08:35 U23025 EasyJet
Milan — Dusseldorf
1h 50m stop
11:55 — 15:20 AY1392 Finnair
Dusseldorf — Helsinki
40m stop
16:25 — 17:50 AY9 Finnair
Helsinki — Chicago
15h 55m
including layover
Find flight
from$416
09:00 — 17:50
09:00 — 11:00 W61432 Wizz Air
Milan — Warsaw
2h stop
13:00 — 15:40 AY1144 Finnair
Warsaw — Helsinki
45m stop
16:25 — 17:50 AY9 Finnair
Helsinki — Chicago
15h 50m
including layover
Find flight
from$412
09:15 — 19:40
08:55 — 10:40 W45018 Aero Services Executive
Milan — Tirana
2h 30m stop
13:30 — 15:35 LO598 LOT
Tirana — Warsaw
1h stop
16:40 — 20:00 LO3 LOT
Warsaw — Chicago
17h 25m
including layover
Find flight
from$590
11:55 — 21:00
11:55 — 13:50 W45024 Aero Services Executive
Milan — Tirana
1h 15m stop
15:05 — 16:05 JU163 Air Serbia
Tirana — Belgrade
1h 15m stop
17:20 — 21:00 JU506 Air Serbia
Belgrade — Chicago
16h 5m
including layover
Find flight
from$579
12:15 — 09:40
+1 day
12:15 — 13:40 FR2285 Ryanair
Milan — Naples
2h 20m stop
16:00 — 19:25 TK1464 Turkish Airlines
Naples — Istanbul
11h 5m stop
06:30 — 09:40 TK185 Turkish Airlines
Istanbul — Chicago
28h 25m
including layover
Find flight
from$746
12:15 — 09:40
+1 day
12:15 — 13:40 FR2285 Ryanair
Milan — Naples
7h stop
20:40 — 00:05 TK1880 Turkish Airlines
Naples — Istanbul
6h 25m stop
06:30 — 09:40 TK185 Turkish Airlines
Istanbul — Chicago
28h 25m
including layover
Find flight
from$746
18:30 — 19:40
+1 day
18:30 — 19:55 FR1533 Ryanair
Milan — Vienna
13h 20m stop
09:15 — 10:30 LO224 LOT
Vienna — Warsaw
6h 10m stop
16:40 — 19:40 LO3 LOT
Warsaw — Chicago
32h 10m
including layover
Find flight
from$748
22:15 — 18:15
+1 day
22:15 — 23:45 EI437 Aer Lingus
Milan — Dublin
9h 5m stop
08:50 — 10:20 EI156 Aer Lingus
Dublin — London
5h 10m stop
15:30 — 18:15 EI8997 Aer Lingus
London — Chicago
27h
including layover
Find flight
from$718
22:15 — 18:15
+1 day
22:15 — 23:45 EI437 Aer Lingus
Milan — Dublin
6h 45m stop
06:30 — 08:00 EI152 Aer Lingus
Dublin — London
7h 30m stop
15:30 — 18:15 EI8997 Aer Lingus
London — Chicago
27h
including layover
Find flight
from$718
23:50 — 15:55
+1 day
23:10 — 00:45 W64124 Wizz Air
Milan — Belgrade
8h stop
09:25 — 11:20 LX1413 SWISS International Air Lines
Belgrade — Zurich
1h 45m stop
13:05 — 15:55 LX8 SWISS International Air Lines
Zurich — Chicago
23h 5m
including layover
Find flight
from$778
*Departure and arrival times - local. Updated on July 30, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 05:25 to 23:59 from 4 Milan airports and arrive 05:25 to 23:59 to 7 Chicago airports. Average flight time is 9h 50m.

  • The fastest flight 9h 50m
  • Average flight time 9h 50m
  • The earliest flight 05:25
  • The latest flight 23:59
  • Distance 4530 ml

The cheapest months to travel to Chicago are august (from 412 $), september (from 449 $), october (from 463 $).

The most expensive months are december (from 665 $), january (from 665 $), november (from 663 $).

What is the lowest airfare Milan to Chicago?

The cheapest plane ticket found by our users is $412. This airfare is for economy class on one-way W61432 flight by Wizz Air for August 28, 2025 which leaves Milan Bergamo (Orio al Serio) in Milan at 09:00 am and arrives at Chicago O'Hare International at 17:50.

Economy class
$412
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Business class
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First class
?
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Popular Airlines on the Route

The flight Milan — Chicago is served by 28 regular airlines and 5 low-cost airlines. Most of the flights on this route are operated by Neos - 4 departures per week at the price of from $ 845 . And the most expensive tickets are offered by United Airlines airline - from $ 1601.

Direct flights

There are 2 nonstop flights on the route. The fastest direct flight is LH7812 by Lufthansa takes 9h 50m and the cheapest is W61432 by Wizz Air for $1530.

  • LH - Lufthansa
    from $1530
    Find
  • UA - United Airlines
    from $1601
    Find
See more direct flights

Connecting Flights

There are 152 flights with layovers on the route. The fastest connecting flight is AF1213 by Air France takes 12h 15m and the cheapest is W61432 by Wizz Air for $412.

  • NO - Neos
    from $845
    Find
  • LO - LOT
    from $909
    Find
  • VY - Vueling
    from $966
    Find
  • FI - Icelandair
    from $1064
    Find
  • JU - Air Serbia
    from $1111
    Find
  • FR - Ryanair
    from $724
    Find
  • LX - SWISS International Air Lines
    from $919
    Find
  • A3 - Aegean Airlines
    from $826
    Find
  • DY - Norwegian
    from $719
    Find
  • SK - SAS
    from $776
    Find
  • IB - Iberia
    from $449
    Find
  • KL - KLM
    from $779
    Find
See more connecting flights

Airports

You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).

Milan airports

  • Linate-LIN
    from $423
    Find
  • Malpensa-MXP
    from $416
    Find
  • Milan Bergamo (Orio al Serio)-BGY
    from $412
    Find
  • Segrate-SWK
    Find

Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
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  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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